Yellow azo dyestuff



Patented Au 30, 1932 UNITED STATES PATENT orricu HEINZ EICHWEDE ANDJOSEPH RAOHOR, OF FRANKFOET-ON-THE-MAIN-HOGHST, GERMANY, ASSIGNOR-S TOGENERAL ANILINE WORKS, INC., 0]! NEW YORK, N. Y.,

A COPORATION OF DELAWARE YELLOW. AZO DYEST'UFF No Drawing. Applicationfiled August 27, 1928, Serial No. 302,436, and in Germany September 19,1927.

This invention relates to new yellow azo dyestuffs, more particularly toazo dyestuffs of the following general formula:

wherein X stands for -OH OOOI-l or COO-alkyl and R represents a phenylnucleus which may be substituted by alkyl, oxalkyl, the sulfonic acid orthe carboxylic acid roup.

We have found that dyestuffs of excellent fastness properties areobtainable by coupling the diazo compound of a base of the generalformula:

wherein the two aryl residues may be substituted or not, with apyrazolone of the general formula N..- Hzr0( wherein X stands for CHCGOH or COO- allryl and R represents a phenyl nucleus which may besubstituted by alkyl, O-allryl, the sulfonic acid or the carboxylic acidgroup.

W hen using as coupling components nonsulfona-ted pyrazolones thedyestufis may subsequently be sulfonated. The new dyestuffs possess verygood properties as to fastness to washing, fulling and light and can beused according to their composition as wool dyestuffs, for silk andartificial silk or as lake dyestuffs.

The following example illustrates the invention, it being understoodthat it is in no way limitative. The parts are by weight:

26.2 parts of meta-aminobenzenesulfonic acid methylphenylaniide arediazotized with 4:8 parts of hydrochloric acid of 20 Be. and 6.9 partsof sodium nitrite, and the diazo compound is coupled with 27 .6 parts ofthe sodium salt of l-(l-sulfophenyl) -8-mcthyl-5-pyrazolone in thepresence of an excess of sodium carbonate. The resulting dyestuil ispreci itated by the addition of sodium chloride and filtered. It dyeswool yellow tints of excellent fastness to washing, fulling and light.It has the following formula:

I OH

The 'meta-aminobenzenesulfonic acid methylphenylamide of the formula:

( lHa used as starting material may, for instance, be prepared bymethylating and reducing to. condensation product from meta-nitroben-Zenesulfonic acid chloride and aniline or by reducing the condensationproduct from meta-nitrobenzenesulfo chloride and methyl aniline.

Similar dyestuffs are obtained by substituting for themeta-aminobenzenesulfo-acidmethylphenylamide for instancemeta-aminobenzenesulfonic-acid ethylphenylamide, or

pa-ra-aminotoluene ortho sulfonic-acid-mewherein X stands for CH COOH orCOG-allryl, being yellow powders dyeing the material yellow shades ofgood fastness properties.

2. As a new product, the azo dyestuff of the following general formula:

- H3CC=N -o2s N SOaNa OHa tures.

being a yellow powder dyeing wool ellow tints of excellent fastness towashing, ulling and light.

3. As new products the azo dyestufi's of the following general formula:

I \N-R ary1N-0zSaryl- N=NG=O alkyl (IJH wherein X stands for CH COOH orCOO-alkyl and wherein R represents a phenyl nucleus which may besubstituted by alkyl, O-alkyl, the sulfonic acid or the carboxylic acidgroup and wherein aryl represents a benzene residue, the said newproducts being yellow powders yielding dyeings of yellow shades and ofgood fastness properties. I

4. As new products the azo dyestuffs of the following general formula:

4 W SO;Na myllTIO;S-Q I B alkyl d 6H wherein X stands for CH -COOH or-COO-alkyl and wherein aryl represents a benzene residue the saidproducts being yellow powders yielding dyeings of yellow shades and ofgood fastness properties.

5. As new products the azo dyestufils of the following general formula:

being yellow powders yielding dyeings of yellow shades and of goodfastness properties.

6. As new products, the azo dyestuffs of the following general formula:

wherein X stands for -CH or COOH and wherein R represents a phenylnucleus which is substituted by the sulfonic acid group and wherein arylrepresents a benzene residue. 7 As new products, the azo dyestuffs ofthe following formula:

wherein aryl represents a benzene residue.

In testlmonywhereof, we afiix our signa- I HEINZ EICHWEDE. JOSEPHRACHOR.

